Synthesis and androgen effects of 7 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one, 5 alpha-androstan-3 alpha,7 alpha,17 beta-triol and 5 alpha-androstane-3 beta,7 alpha,17 beta-triol.
The steroids 7 alpha,17 beta-dihydroxy-5 alpha-androstan-3-one (7 alpha-hydroxy-Dht), 5 alpha-androstan-3 alpha,7 alpha,17 beta-triol (7 alpha-hydroxy-3 alpha-A'DIOL) and 5 alpha-androstane-3 beta,7 alpha,17 beta-triol (7 alpha-hydroxy-3 beta-A'DIOL) have been synthetized from 7 alpha,17 beta-dihydroxy-4-androsten-3-one (7 alpha-hydroxy-testosterone). The effect of administering 7 alpha-hydroxy-Dht, 7 alpha-hydroxy-3 alpha-A'DIOL or 7 alpha-hydroxy-3 beta-A'DIOL on serum levels of LH, FSH and on ventral prostate and seminal vesicle weight were investigated in gonadectomized adult male rats. Each steroid was administered for seven days in a dose of 300 micrograms per day. No suppression of serum LH or FSH levels was recorded following injections of these 7 alpha-hydroxylated steroids to castrated rats, compared to castrated control rats receiving vehicle only. Administration of 7 alpha-hydroxy-Dht or 7 alpha-hydroxy-3 alpha-A'DIOL to castrated mature rats could maintain ventral prostate and seminal vesicle weights above that of castrated control rats. Administration of 7 alpha-hydroxy-3 beta-A'DIOL to castrated mature rats resulted in ventral prostate weights slightly above castrate control levels, while seminal vesicle weight in such rats were in the same range as castrated control rats. Intraperitoneal administration of testosterone or of 5 alpha-androstane-3 beta,17 beta-diol (3 beta-A'DIOL) to castrated rats maintained activity of the androgen dependent isoenzyme of acid phosphatase in the ventral prostate; 7 alpha-hydroxy-testosterone or 7 alpha-hydroxy-3 beta-A'DIOL showed, however, no effect on this enzymic activity.
D015113:Androstane-3,17-diol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D000732:Androstanols / Q000494:pharmacology*; D000818:Animals; D001681:Biological Assay; D002369:Castration; D005640:Follicle Stimulating Hormone / Q000097:blood*; D006915:Hydroxytestosterones / Q000138:chemical synthesis / Q000494:pharmacology*; D007986:Luteinizing Hormone / Q000097:blood*; D008297:Male; D009929:Organ Size / Q000187:drug effects; D011467:Prostate / Q000033:anatomy & histology*; D051381:Rats; D011919:Rats, Inbred Strains; D012669:Seminal Vesicles / Q000033:anatomy & histology*; D013739:Testosterone / Q000031:analogs & derivatives*
D000732:Androstanols; D006915:Hydroxytestosterones; C034823:7-hydroxydihydrotestosterone; C015680:androstane-3,7,17-triol; D015113:Androstane-3,17-diol; D013739:Testosterone; D007986:Luteinizing Hormone; D005640:Follicle Stimulating Hormone